Benzyl Bromide → benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-beta-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-alpha-D-glucopyranoside

HRID 1074432노트

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HRID 1074432 반응식
[C:1]([NH:4][C@@H:5]1[C@@H:18]([O:19][CH2:20][CH:21]=[CH2:22])[C@H:17]([O:23][C@@H:24]2[O:31][C@H:30]([CH2:32][OH:33])[C@@H:28]([OH:29])[C@H:26]([OH:27])[C@H:25]2[NH:34][C:35](=[O:37])[CH3:36])[C@@H:16]([CH2:38][O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[O:15][C@@H:6]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2].[O-2].[Ba+2].O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].[CH2:60](Br)[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>CN(C)C=O.C(Cl)(Cl)Cl>[C:1]([NH:4][C@@H:5]1[C@@H:18]([O:19][CH2:20][CH:21]=[CH2:22])[C@H:17]([O:23][C@@H:24]2[O:31][C@H:30]([CH2:32][O:33][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C@@H:28]([O:29][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C@H:26]([O:27][CH2:60][C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[C@H:25]2[NH:34][C:35](=[O:37])[CH3:36])[C@@H:16]([CH2:38][O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[O:15][C@@H:6]1[O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:3])[CH3:2]

참가 물질

7

반응물 4

HCID 7498Benzyl Bromide2회HCID 9855530Barium Oxide Nanoparticle Dispersion2회HCID 14129571benzyl 2-acetamido-4-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-alpha-D-glucopyranosideHCID 17749109Barium hydroxide, octahydrate2회

생성물 1

HCID 10930998benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-beta-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-alpha-D-glucopyranoside

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of benzyl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside (624 mg, 0.97 mmol) in N,N-dimethylformamide (15 ml) are added barium oxide (670 mg), barium hydroxide octahydrate (223 mg), and benzyl bromide (1.04 ml, 8.74 mmol). The reaction mixture is stirred for 20 hours at room temperature at which time additional barium oxide (335 mg), barium hydroxide octahydrate (112 mg) and benzyl bromide (0.52 ml) are added. Stirring is continued for 24 hours at room temperature. The reaction mixture is then diluted with chloroform (100 ml), washed successively with 60% aqueous acetic acid, saturated sodium bicarbonate, and water, dried (sodium sulfate), and evaporated. The residue is applied to a column of silica gel (90 g) that is eluted with 4:1 chloroform-ethyl acetate. Combination and evaporation of the appropriate fractions affords benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside as a white solid; yield 612 mg (69%), [α]D25 +58° (c, 1.1, chloroform). The 300 MHz nmr spectrum in chloroform-d is in accord with the desired structure.

후처리

  1. additionare added
  2. washwashed successively with 60% aqueous acetic acid, saturated sodium bicarbonate, and water
  3. dry with materialdried (sodium sulfate)
  4. customevaporated
  5. washis eluted with 4:1 chloroform-ethyl acetate
  6. customCombination and evaporation of the appropriate fractions

출처 및 근거

ORD 기록
ord-8644e4ae5eaf45abbb4da122641b8472
출처 데이터셋
uspto-grants-1983_07
특허 번호
US04391800

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